Tert-butyldicarbonate → HCID 58910006, compound

HRID 1296033Notes

Reaction equation

HRID 1296033 reaction equation
[CH3:1][NH:2][C:3](=[O:34])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([CH2:11][NH:12][CH2:13][C:14]([C:16]2[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:19]([OH:26])=[C:18]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:17]=2)=[O:15])=[CH:6][C:5]=1[O:31][CH2:32][CH3:33].[C:35](OC([O-])=O)([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>O1CCCC1>[Br:10][C:8]1[CH:9]=[C:4]([C:3]([NH:2][CH3:1])=[O:34])[C:5]([O:31][CH2:32][CH3:33])=[CH:6][C:7]=1[CH2:11][N:12]([CH2:13][C:14]([C:16]1[CH:17]=[C:18]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:19]([OH:26])=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)=[O:15])[C:35](=[O:36])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 22064466Tert-butyldicarbonateHCID 58909955HCID 58909955, compound

Product 1

HCID 58910006HCID 58910006, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving the N1-methyl-5-bromo-4-[({2-[3,5-di(tert-butyl)-4-hydroxyphenyl]-2-oxoethyl}amino)methyl]-2-ethoxybenzamide (1.75 g) in tetrahydrofuran (20 ml), tert-butyl dicarbonate (770 mg) was added. The mixture was heated to reflux for 2 hours, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1.97 g) as a white solid.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 2 hours
  4. concentrationthe reaction mixture was concentrated
  5. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c6533298e1ad4431b4fc6c93ecdb5c50
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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